Professor of Chemistry
About
Research in our group is focused primarily upon the development of new strategies and methodologies for the synthesis of natural products. Of particular interest are the discovery of practical new processes which utilize the redox chemistry of visible light activated metal complexes. Visible light sensitization is an attractive means to initiate organic reactions due to the lack of visible light absorbance by organic compounds thereby reducing the side reactions that are often associated with photochemical reactions conducted with high energy UV light. These photocatalysts offer a means to selectively functionalize organic molecules with the appropriate choice of an excited state quencher. These processes offer improved chemoselectivity (and strategic advantages when employed in total synthesis) over current approaches while also enabling the reduction of stoichiometric waste byproducts. In particular, we are focusing our efforts in the following areas: (1) the development of new methodologies based upon visible light initiated electron transfer reactions; (2) applications of these methods to complex natural product synthesis; (3) technology-enabled reaction discovery and photocatalysis using mesoflow and microfluidics chemistry; and (4) new approaches to biomass conversion.
Representative Publications
J.D. Nguyen, E.M. D'Amato, J.M.R. Narayanam, C.R.J. Stephenson, "Engaging Unactivated Alkyl, Alkenyl and Aryl iodides in Visible-Light Mediated Free Radical Reactions." Nature Chem. 2012, 4, 854.
C.-J. Wallentin, J.D. Nguyen, P. Finkbeiner, C.R.J. Stephenson, "Visible Light-Mediated Atom Transfer Radical Addition via Oxidative and Reductive Quenching of Photocatalysts." J. Am. Chem. Soc. 2012, 134, 8875.
J.W. Tucker, Y. Zhang, T.F. Jamison, C.R.J. Stephenson, "Visible-Light Photoredox Catalysis in Flow." Angew. Chem. Int. Ed. 2012, 51, 4144.
J.D. Nguyen, J.W. Tucker, M.D. Konieczynska, "Intermolecular Atom Transfer Radical Addition to Olefins Mediated by Oxidative Quenching of Photoredox Catalysts." J. Am. Chem. Soc. 2011, 33, 4160.
C. Dai, J.M.R. Narayanam, C.R.J. Stephenson, "Visible-light-mediated conversion of alcohols to halides." Nature Chem. 2011, 3, 140.
L. Furst, J.M.R. Narayanam, C.R.J. Stephenson, "Total Synthesis of (+)-Gliocladin C Enabled by Visible-Light Photoredox Catalysis." Angew. Chem. Int. Ed. 2011, 50, 9655.
A.G. Condie, J.C. Gonzalez-Gomez, C.R.J. Stephenson*, "Visible Light Photoredox Catalysis: Aza-Henry Reactions via C?H Functionalization." J. Am. Chem. Soc. 2010, 132, 1464.
J.M.R. Narayanam; J.W. Tucker; C.R.J. Stephenson*, "Electron-Transfer Photo-Redox Catalysis: Development of a Tin-Free, Reductive Dehalogenation Reaction" J. Am. Chem. Soc. 2009, 131, 8756.
Awards
Dreyfus Teacher-Scholar Award 2013
Eli Lilly Grantee Award 2013
Novartis Early Career Award in Organic Chemistry 2012
Alfred P. Sloan Research Fellow 2011
Amgen Young Investigator Award 2011
NSF Career Award 2011
Boehringer-Ingelheim New Investigator Award 2010
Thieme Synthesis/Synlett Journal Award 2009
Research Areas(s)
- Bioorganic Chemistry
- Energy Science
- Organic Chemistry
- Organometallic Chemistry
- Sustainable Chemistry
- New Methods Development, Catalysis
- Complex Molecule Synthesis
